NP-MRD: Showing NP-Card for 3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid (NP0328425)

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Record Information

Version

2.0

Created at

2022-09-12 11:53:15 UTC

Updated at

2022-09-12 11:53:15 UTC

NP-MRD ID

NP0328425

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid

Description

3-Hydroxy-2-[(1-hydroxyethylidene)amino]-N-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. 3-Hydroxy-2-[(1-hydroxyethylidene)amino]-N-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
    4.9917    2.0434    1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    1.1354    0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1334    0.8962    1.8682 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544    0.5782   -0.3736 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992   -0.2936   -0.7582 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7540   -1.7376   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8650   -2.1501   -1.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2024    0.1893   -0.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1812    1.2820    0.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0026   -0.5569   -0.3697 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2443   -0.0665    0.1627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2096    0.2278   -0.9507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1603   -0.6971   -1.9913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5956    0.4473   -0.4851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8101    1.9419   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0104   -0.2234    0.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543   -1.2694    1.0385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4433   -2.4440    0.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049   -0.9603    1.2403 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6242   -0.4029    2.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    1.7944    0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6607    3.0794    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4452    1.9005    2.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356    0.8416   -1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3489   -0.1260   -1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9283   -2.4033   -0.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319   -1.9571    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954   -1.7000   -1.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0081   -1.4601   -0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0327    0.9176    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8498    1.1922   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143   -1.5696   -1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2966    0.2143   -1.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8926    2.1503   -0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2924    2.4701   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3346    2.1888    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.5547    2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2156   -2.3011   -0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2666   -1.9489    1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3072    0.3321    2.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  5  1  0
  5  6  1  0
  6  7  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 14 33  1  6
 17 37  1  1
 18 38  1  0
 19 39  1  1
 20 40  1  0
 11 30  1  1
 10 29  1  0
  5 25  1  6
  6 26  1  0
  6 27  1  0
  7 28  1  0
  4 24  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 12 31  1  6
 13 32  1  0
M  END


  Mrv1533004241500102D          

 20 20  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  8 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(O)C(O)C(NC(=O)C(CO)NC(C)=O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H20N2O7/c1-4-8(16)7(9(17)11(19)20-4)13-10(18)6(3-14)12-5(2)15/h4,6-9,11,14,16-17,19H,3H2,1-2H3,(H,12,15)(H,13,18)

> <INCHI_KEY>
VICBTWWDBMAFMD-UHFFFAOYSA-N

> <FORMULA>
C11H20N2O7

> <MOLECULAR_WEIGHT>
292.288

> <EXACT_MASS>
292.127050992

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.079848549420763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-acetamido-3-hydroxy-N-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanamide

> <ALOGPS_LOGP>
-2.20

> <JCHEM_LOGP>
-3.7570934090000003

> <ALOGPS_LOGS>
-0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.041277339953886

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.252535067242407

> <JCHEM_PKA_STRONGEST_BASIC>
-2.006080943425905

> <JCHEM_POLAR_SURFACE_AREA>
148.35

> <JCHEM_REFRACTIVITY>
64.3221

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamido-3-hydroxy-N-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       8.002   3.080   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    8    2   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-2-[(1-hydroxyethylidene)amino]-N-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidate	Generator

Chemical Formula

C₁₁H₂₀N₂O₇

Average Mass

292.2880 Da

Monoisotopic Mass

292.12705 Da

IUPAC Name

2-acetamido-3-hydroxy-N-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanamide

Traditional Name

2-acetamido-3-hydroxy-N-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanamide

CAS Registry Number

Not Available

SMILES

CC1OC(O)C(O)C(NC(=O)C(CO)NC(C)=O)C1O

InChI Identifier

InChI=1S/C11H20N2O7/c1-4-8(16)7(9(17)11(19)20-4)13-10(18)6(3-14)12-5(2)15/h4,6-9,11,14,16-17,19H,3H2,1-2H3,(H,12,15)(H,13,18)

InChI Key

VICBTWWDBMAFMD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Hexose monosaccharide
Serine or derivatives
Monosaccharide
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.2	ALOGPS
logP	-3.8	ChemAxon
logS	-0.55	ALOGPS
pKa (Strongest Acidic)	11.25	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	148.35 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	64.32 m³·mol⁻¹	ChemAxon
Polarizability	28.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid (NP0328425)

MOL for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)

3D MOL for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)

3D SDF for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)

3D-SDF for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)

PDB for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)

3D PDB for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)

SMILES for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)

INCHI for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)

Structure for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)

3D Structure for NP0328425 (3-hydroxy-2-[(1-hydroxyethylidene)amino]-n-(2,3,5-trihydroxy-6-methyloxan-4-yl)propanimidic acid)